Aryl sulfonyl fluoride synthesis via palladium-catalyzed fluorosulfonylation of aryl thianthrenium salts

Lingling Shan; Zhanhu Ma; Caiyun Ou; Yinxia Cai; Yuyang Ma; Yong Guo; Xiaoyu Ma; Chao Liu

doi:10.1039/d3ob00462g

Aryl sulfonyl fluoride synthesis via palladium-catalyzed fluorosulfonylation of aryl thianthrenium salts

Org Biomol Chem. 2023 May 10;21(18):3789-3793. doi: 10.1039/d3ob00462g.

Authors

Lingling Shan¹, Zhanhu Ma¹, Caiyun Ou¹, Yinxia Cai¹, Yuyang Ma¹, Yong Guo², Xiaoyu Ma¹, Chao Liu^{1

2}

Affiliations

¹ School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, China. maxiaoyu@sit.edu.cn.
² Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

PMID: 37099401
DOI: 10.1039/d3ob00462g

Abstract

We developed an efficient palladium-catalyzed fluorosulfonylation reaction of aryl thianthrenium salts to smoothly prepare various aryl sulfonyl fluorides using cheap Na₂S₂O₄ as a convenient sulfonyl source in combination with N-fluorobenzenesulfonimide (NFSI) as an ideal fluorine source under mild reduction conditions. A one-pot synthesis of aryl sulfonyl fluorides starting from various arenes was established as well without the need for separating aryl thianthrenium salts. The practicality of this protocol was demonstrated by gram-scale synthesis, derivatization reactions, and excellent yields.